Enantiospecific Synthesis of Trisubstituted Butyrolactone Natural Products and Their Analogs
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (22) , 7848-7855
- https://doi.org/10.1021/jo961171i
Abstract
A general methodology for the synthesis of highly substituted butyrolactones in enantiomerically pure form has been developed. The application of this process in a highly efficient synthesis of lactone natural products blastmycinone (1), NFX-2 (2), antimycinone (3), and NFX-4 (4) and two lipid metabolites (5, 6) are described. Additionally, the total synthesis of 5-epi-blastmycinone (22), 5-epi-NFX-2 (21b), 5-epi-NFX-4 (21c), and lipid metabolite analogs (19, 20) are also described. The overall yields for the target molecules are the highest reported so far in the literature.Keywords
This publication has 34 references indexed in Scilit:
- Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutionsThe Journal of Organic Chemistry, 1993
- A convergent, highly stereoselective synthesis of a C-11-C-21 subunit of the macbecinsThe Journal of Organic Chemistry, 1991
- Novel Asymmetric Synthesis of γ-Alkylated Lactones via Successive Alkylation and Reduction of Chiral Cyclic Imides with C2-SymmetryChemistry Letters, 1991
- Total synthesis and structural investigations of didemnins A, B, and CJournal of the American Chemical Society, 1990
- Preparation of Enantiomerically Enriched Compounds Using Enzymes; VII.1A Synthesis of Japanese Beetle Pheromone Utilizing Lipase-Catalyzed Enantioselective LactonizationSynthesis, 1990
- Synthesis of Optically Active Litsenolide CChemistry Letters, 1987
- ACYCLIC STEREOSELECTION USING RELATIVE 1,2-ASYMMETRIC INDUCTION. SELECTIVE SYNTHESIS OF (+)-BLASTMYCINONEChemistry Letters, 1985
- A series of (2S)-2-O-protected-2-hydroxypropanals (L-lactaldehydes) suitable for use as optically active intermediatesThe Journal of Organic Chemistry, 1983
- γ-Lactones from Iryanthera speciesPhytochemistry, 1983
- The Chemistry of Antimycin A. X. Structure of the Antimycins1Journal of the American Chemical Society, 1961